Many information processing systems are configured to transfer files from data sources to various destinations over a network. However, issues can arise in conjunction with such file transfers. For example, in the case of usage data files or other types of files automatically generated by information technology (IT) products currently deployed in cloud-based or enterprise-based information processing systems, it can be difficult to determine file transfer status, estimated time of file transfer completion, file transfer success or failure, and other related file transfer information. Moreover, such information is not made accessible to users, thereby necessitating various types of manual intervention such as a user manually checking a transferred file to confirm that its size matches an expected file size.